Almost Fearless

Becoming a Digital Nomad, Freelance Edition: Day 16 of 30w30d

This post is part of 30 Ways in 30 days to Redesign Your Life and Travel the World. This series seeks to give you the practical, real world steps you need to take to get from wherever you are, to exactly where you want to be– traveling the world and living the lifestyle you want.


30 ways in 30 days, digital nomad, freelance, your own boss, online travel

On Day 3, we talked about Turning Your Job Digital.  But what if your boss won’t agree to allow you to work 100% remotely or your currently job doesn’t translate well to a digital one–or more importantly, you just don’t want to keep doing what you’re doing now.  Option #2: Going Freelance.

Going freelance is the path of least resistance.   You don’t need permission from your boss or start-up money or even a complicated legal structure.  This makes it really easy for people enter the marketplace– making it extremely competitive.  The good news is that most freelancers are horrible.  If you’re good, savvy and work hard it’s still possible to make room for yourself.

Which Comes First the Website or the Client?

The first thing everyone does when starting out is to spend a month building a web presence.  I say, wait.  The most important thing to becoming a freelancer is getting work.  Presuming you have some experience, have some people you have worked with and can speak positively to your experience–  you already have your first line of attack: the referral.  If you’re not so great at networking, now is the time to start.  Set up a LinkedIn account and feed it the emails of all your former coworkers (or let it access your email and grab your whole address book). Now is not the time to spam everyone you know, but it is the time to put yourself out there.

Getting work without a website

  1. LinkedIn is your friend. Mine your network.  Remember that old boss that loved working with you?  These are potential clients.
  2. Use online sites like or to hawk your skills.
  3. Check out the Work Wirelessly job board and search for postings.
  4. Create a profile that specifies remote only.  (You might get contacted by a lot of headhunters–depending on your skill set– but they often have short term contract work).
  5. Go Local.  You’d be surprised how the online world neglects the businesses right in your home town.
  6. Find the consulting firms/artists agencies/placement agencies for your niche.  Sometimes they can throw you higher profile work than you’d get on your own.
  7. If appropriate, start attending networking events in your area or participating on conferences to get your name out there.

Once you get the work, then the fun begins.

Three Ways to Be a Kick Ass Freelancer

  1. Know what you’re doing
  2. Do it and on time
  3. Be a professional

Being a professional is the toughest one, because it’s so subjective.  I think of it as emulating this kind, helpful, honest person who is both confident and excited but practical and realistic (even when you feel like strangling your client).  It comes with practice and most of it is learned from being on the receiving end of someone who is clearly not professional.

Everything you say and do should have the underlying message: I am here to help and I’m happy to do it.  Even when you’re delivering a “no”.  A helpful analogy I learned in my corporate training (and believe me there was plenty) was to “Sandwich Your No”.  One layer compassionate understanding, a middle layer of heck no and and bottom crust of I really understand and maybe this will work instead.  An example would be:

  • I understand that it’s important to have this done by Monday.
  • Unfortunately, I’m not going to be able to accommodate your request as I have prior commitments.
  • What can we do now to prepare, so that I can hit the ground running next week?

It sounds cheesy, but seriously it’s like a Jedi-mind trick for pouty clients.  “Oh you understand my needs but aren’t able to meet them but are trying to do whatever you can to help?  Ok.”

The Business Side of Being Your Own Business

You don’t need anything at first, except very good records.  Extremely good, detailed records, with receipts.  For everything.  If you get any money, write it down.  If you spend any money, write it down.  Your home office is a deduction, including the cost of rent and utilities, prorated based on square feet.  Industry publications and memberships can be deductions.  One person I knew went to Italy every year for “research”. Anything could be a deduction, and when you’re filing taxes  you will be absolutely scrambling if you didn’t keep track all year.

Being a sole proprietor under your own tax number (social security) is fine for now (or you can purchase a Tax ID for a few bucks, but you’re still a sole proprietorship, it just prevents you from having to disclose your social to clients).  You don’t need to pursue a LLC or S-Corp legal status yet, you can do it later: it costs money and makes filing your taxes more difficult.  There are benefits, but only if you’re making money!  If you’re pulling in less than $1000 a month, then your deductions will probably be enough to prevent you from paying any real taxes– so why go through all that until it makes sense (i.e. will save you money)?

Why Freelancers Give Up: The Client Cycle

The hardest part of being a freelancer is that it takes almost all of your time to find work.  You might work for 2 months sending out bids, contacting people, surfing the job boards.  Nothing.  Then one day you will get 5 clients at the same time and work around the clock for two months.  Yeah!  You’re finally taking off.  You’ve made it.  Then the work ends, you finally look up and there’s no one around.  There’s absolutely no work.

Limiting the Boom and Bust Cycle of Freelancing

I said limiting, because it’s never possible to have perfectly consistent levels of work.  There will be times when you scramble.  There will be times when your phone is unnaturally quiet.

Golden rule of freelancing: Always be looking for new work.  Even when you’re working, even when you can’t breathe, you need to keep putting yourself out there.

But, you can’t say ‘yes’ to everyone.  You can’t accommodate last minute requests all the time.  You can’t take a project when you’re overbooked just because you’re afraid another one won’t come.  You will burn out, you will disappoint people when you under-perform and in a year from now you’re not going to like freelancing very much.

Too much work?

Negotiate later start dates. I know the client said it has to be done by X, but they are full of crap (usually).  Every client in the world says that because they think it prevents you from taking forever on it.  Be firm.  Set expectations.

If you’re going to lose the account anyway, pass it to a friend. You have to say no sometimes, but giving a referral buys you enormous goodwill and it’s just the nice thing to do.  Maybe they’ll repay the favor.

Raise your prices. If you’re consistently working at 90%, you’re undercharging.  You will lose some clients, but that’s the point.  It’s basic economics.  There is one of you (limited supply) and a high demand (many clients) which means prices have to go up.  Be strong!  You’re obviously worth it.

Fire your annoying clients. If they take up a lot of time for the same price as your appreciative, nice clients, then fire their butt.  They will never improve, they will always be a pain, so might as well cut them loose now, while you have plenty of good work to take their place.

You Can Start Now

If you’re still at the day job, there’s no reason that you can’t begin looking for clients now. It maybe difficult to manage after hours work, but it’s a really smart idea to have at least a few clients before you take the plunge.  If you think your boss will mind, don’t talk about it on Facebook or LinkedIn, if you have current coworkers as friends.  It may mean a little stealth work, setting up new profiles under a new email, just to keep things separate.

Ultimately, there’s a million things to be learned about freelancing, but it all starts with you, getting out there, getting work and keeping clients.

Additional Reading:

10 Tips for Becoming a Freelancing PowerHouse

10 Reasons Why Freelancing is the Best Job Security

Freelancers’ Guide to Getting Paid—on Time

Is Freelancing Right For You?

The Buffy the Vampire Slayer Guide to Freelancing

pic based on:doctabu

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”



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